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5244 WINDING WAY Sarasota, FL 34242

Pending

UPDATED:

$ 1,250,000
5244 WINDING WAY Sarasota, FL 34242
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Sarasota, FL 34242,5244 WINDING WAY
Sarasota, FL 34242,5244 WINDING WAY
Sarasota, FL 34242,5244 WINDING WAY
Sarasota, FL 34242,5244 WINDING WAY
Sarasota, FL 34242,5244 WINDING WAY
Sarasota, FL 34242,5244 WINDING WAY
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Rich Henderson

Rich Henderson

rich@myrealtorrich.com +1(630) 338-3792
$ 1,250,000
Est. payment | /mo

4 Beds

4 Baths

2,100 SqFt


Save Virtual Tour
$ 1,250,000
Est. payment | /mo
Save Virtual Tour

4 Beds

4 Baths

2,100 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Pending

Purchase Type For Sale

Square Footage 2,100 sqft

Price per Sqft $595

Subdivision Twin Oak Pond

MLS Listing ID A4669581

Bedrooms 4

Full Baths 4

HOA Y/N No

Year Built 1967

Annual Tax Amount $9,776

Lot Size 9,583 Sqft

Acres 0.22

Property Sub-Type Single Family Residence

Source Stellar MLS

Property Description

Expansive Coastal Modern Property in a Serene and Peaceful Setting, Seconds to Siesta Key Beach ** 4 Bedrooms, 4 Full Baths with Detached Studio/ADU above the 3 Car Garage (5 Total Bedrooms, 5 Bathrooms) ** Gorgeous Pool among Lush Native Landscape ** NEW ROOF! There is no better value on Siesta Key for your primary occupancy or 2nd home with opportunities to cash flow this investment. The entire property has been updated with wood-looking vinyl, interior/exterior paint, custom baseboard and trim, contemporary lighting fixtures, modern fans and fresh marcite in the refinished pool. The studio provides new vinyl windows and a mini-split AC unit for energy efficient climate controlling of this private space. You will love the floor plan of both the main house and studio! The main house provides a great room concept with an abundance of joyful natural light and multiple sets of French doors leading to the pool. Each bedroom receives a private bath with 2 primary suites enjoying idyllic views of the pool and tropical landscape. Simply stated, this estate property is meant for hosting large groups, comfortably. Located inside the charming Canopy Roads of Twin Oak, this beach property is private, serene and inspiring. Live by the beach, but away from the noise. The good life is found here

Location

State FL

County Sarasota

Community Twin Oak Pond

Area 34242 - Sarasota/Crescent Beach/Siesta Key

Zoning RSF3

Interior

Interior Features Kitchen/Family Room Combo, Open Floorplan, Solid Surface Counters, Walk-In Closet(s)

Heating Central

Cooling Central Air, Mini-Split Unit(s)

Flooring Ceramic Tile, Vinyl

Fireplace false

Appliance Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer

Laundry Inside, Other

Exterior

Exterior Feature French Doors

Garage Spaces 3.0

Pool Gunite, In Ground

Utilities Available BB/HS Internet Available, Cable Connected

Roof Type Shingle

Attached Garage false

Garage true

Private Pool Yes

Building

Entry Level Two

Foundation Crawlspace

Lot Size Range 0 to less than 1/4

Sewer Public Sewer

Water Public

Structure Type Wood Siding

New Construction false

Others

Pets Allowed Yes

Senior Community No

Ownership Fee Simple

Acceptable Financing Cash, Conventional

Membership Fee Required Optional

Listing Terms Cash, Conventional

Special Listing Condition None

Virtual Tour https://www.propertypanorama.com/instaview/stellar/A4669581

Stellar MLS
© 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved.
Listed by Justin Shirley SHIRLEY INTERNATIONAL REALTY
Schools and Properties Nearby
SCHOOLSPROPERTIES
Elementary Schools 8
  • 9

    Southside Elementary School

    Public | PK - 5

  • 8

    Phillippi Shores Elementary School

    Public | PK - 5

  • 7

    Gulf Gate Elementary School

    Public | PK - 5

  • 0

    Ese Special Programs

    Public | PK - 12

  • 0

    Sarasota Virtual Instruction Program

    Public | KG - 12

  • 0

    The Out-of-Door Academy

    Private | PK - 12

  • 0

    Out of Door Academy-Upper School

    Private | PK - 12

  • 0

    Incarnation Catholic School

    Private | PK - 8

Middle Schools 1
  • 7

    Brookside Middle School

    Public | 6 - 8

High Schools 2
  • 7

    Riverview High School

    Public | 9 - 12

  • 0

    Sarasota Virtual Instruction (Course Offerings)

    Public | 9 - 12

  • 5225 HIDDEN HARBOR RD, Sarasota, FL 34242

    0.61 Acres

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    4 Beds 5 Baths 4,254 SqFt

    Single Family Home

    Listed by Bradley Kayser COLDWELL BANKER REALTY
  • 5155 HIDDEN HARBOR RD, Sarasota, FL 34242

    3 Beds 3 Baths 2,233 SqFt

    Single Family Home

    Listed by Matt Buttner LIST NOW REALTY, LLC
  • 5132 JUNGLE PLUM RD, Sarasota, FL 34242

    5 Beds 7 Baths 6,928 SqFt

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  • 5362 SHADOW LAWN DR, Sarasota, FL 34242

    3 Beds 5 Baths 4,294 SqFt

    Single Family Home

    Listed by Morgan Marziali NCC PROPERTIES LLC
  • 5502 SHADOW LAWN DR, Sarasota, FL 34242

    3 Beds 4 Baths 2,337 SqFt

    Single Family Home

    Listed by Dan Miller PREFERRED SHORE LLC
  • 5502 SHADOW LAWN DR, Sarasota, FL 34242

    0.33 Acres

    Vacant Land

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There are 1,836 listings nearby.
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Rich Henderson
Rich Henderson

Sales Executive | License ID: SL3522272

rich@myrealtorrich.com

+1(630) 338-3792

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5244 WINDING WAY

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